Red Lipstick
by Kisshulover1
Summary: The 1940's were not the best of times for young Castiel Novak, simply being because he had a secret that according to his family, no seventeen-year old red-blooded American boy should have. But it's not his fault that the only two things in this hateful world than can make him feel beautiful and loved is Dean Winchester and Bright Red Lipstick. It's not his fault. Cross-Dressing .


**Red Lipstick**

…

**This was supposed to be an excerpt for "All in One Basket" but I think it'd do better as a mini fic on it's own. This is for the beautiful anon (Cough - Rachael - Cough), who requested any pairing of my choice in drag. I chose Destiel.**

…

The September wind blew hazy and cool against the glass window pane of Anna's bedroom window, the curtains of lilac colored linen brushed against the glossy frames to create a soft music all their own.

It was just about time in the season when the pears were plucked from their dusty trees and cradled into baskets wrapped heavy with cloth and wicker- and so the room, with the late sunset sun streaking through, smelled fresh and clean like the fruit of the pear. Even Anna's wall paper which was speckled and olive green reminded one pleasantly of the odd shaped fruit, and it brought a smile to the littlest Novak's lips.

Anna's room always smelled sweet, Castiel mused inside the safety and quiet of his own mind as he carefully picked his way over his sisters slightly un-kept room. Sunflower dresses in light blues and jaunty yellows were scattered and wrinkled on the floor. A can of Michael's orange tin shoe polish was opened on her desk, smelling like oil and grape-seed - her brand new chestnut mesh colored shoes gleaming from a fresh polish atop a three legged stool.

His sister always had such lovely things - pretty and delicate things in strong bold colors. In oranges brighter than a pumpkin or chocolates in a subtle yet gorgeous mix like the eggshell from a Rhode-Island Red hen. She had so many colors that Castiel wished he could adorn on his frail and scrawny body - only then might he have a greater bought of confidence that his sister seemed to grant from the clothing she wore. From the fake crystals she poked through her ears, (telling her friend Ruby and Jo that they were real when really she bought them off an ad in the back of a comic book), to the big droopy sun hats that she fit snug over her red curls that shined like wine in the summer sun.

He loved everything she wore. Like the soft shockingly blue shorts she wore last Saturday to the Harvest festival - before Daddy, enraged that his daughter was wearing something so un-Godly, scolded her all the way home till she had to return those pretty shorts back to the store. She was gloomy all day over those shorts.

But it wasn't just the clothes he wished he could have. Not really. He knew the clothes really wouldn't solve much of his low self esteem issues, his anxiety and awful loneliness. He knew it would just give him a little nudge in the hip - to say to himself, I can wear whatever I want _and not have Daddy scream at me. _I can wear whatever I want _and not risk a warning punch on the arm from Michael to beat the sissy-ness out of me_. I can wear whatever I want and _Dean Winchester, the love of my seventeen-year-old life will still want to fish with me on Sundays and maybe even let me kiss him even after I told him my secret those long weeks ago. _Dean still hadn't talked to Castiel or approached him after the littlest Novak confessed his feelings for the other boy. Perhaps it was for the best though…

But the thoughts of everything turning out fine and dandy were hopeless thoughts, because he knew that he would still be chased home from the small five-roomed high school in town by his vicious peers while they spit words like _faggot, queer, _and _homo_ at him.

He knew that if his dad ever caught him with that pink and pearl sewed bow in his messy black locks again, he would be bent over the goat fence and beaten with his fathers belt within an inch of his life.

He knew what would happen if he indulged in his wants just a tiny bit. He knew what would happen if he was caught mumbling about Dean Winchester and his God-Damn tan bronzed skin and freckled face and strong _strong_ arms in his sleep.

He knew what would happen, and yet here he was, in his sisters soft carpeted room (the only room in the house with the ivory plush flooring), picking through her dusty drawers to find that one special thing.

That one little object that made him feel at ease - made him feel okay.

Like he was actually beautiful for who he was and what he was. For who he was and for who he loved and the hopes in that he would be loved back.

The special thing that he held so dear was Anna's bright red _Max Factor _brand lipstick that reminded Castiel of a golden bullet shell more than a stalk of waxed coloring for your lips.

It was red - redder than red. Like a ripe glossy apple in September, or like the chestnut hide of Mr. Singer's old mare that gleamed like burning copper.

It was a color he had always loved.

Carefully, biting his lips till they already became pink and plump naturally - as he had seen Anna do each and every morning before she came down outside where Michael and Luke were waiting with the buckboard for them all to clamor up in for school - his fingers felt the cool metal of the tube of make-up.

Breathing a sigh of relief at the familiar feel, he reached back and held the small metal pipe, no bigger than his index finger, up to his mouth.

In a instant his heart began to beat furiously, his eyes wetting themselves as he blinked back at the small oval mirror in Anna's room - a luxury that all the other girls in town crooned over.

He was paler today, maybe it was from him skipping his lunch today at school in favor of reading under the breech tree outside the classroom. He almost never forgot to eat - but the book of poetry by Walt Whitman was just too suburb to resist. As if someone was writing words on the yellowed pages that he himself could understand - like a secret poem of love for him because he was different.

Castiel sighed, noting with a small flash of annoyance that his hand was trembling. He knew no one would come in - Anna was on the front porch nursing a tall glass of ice tea and listening to Gabriel attempt to play the Banjo. He could hear the awful twang of his brothers instrument as he plucked at it. Anna wouldn't be back until the sun had fully dipped below the Alabama swamps and Gabriel had ceased his screeching of off-tuned lyrics.

Parting his lips, trying to keep them relaxed and not in that chapped thin tight line that Gabriel always teased him for - saying he looked like an old man pondering the Universe - Castiel brought the wax tip to his lips and brushed them over once, twice, thrice like he had practiced everyday with his fingers before he went to bed.

In a few seconds of careful sculpting and painting, his lips finally shown a vibrant crimson that polished his mouth and made his nicely brushed teeth even that much more whiter.

He looked beautiful, he admitted. If it wasn't too vain for him to say. He was the son of a Preacher man after all. One could only get so far with vanity.

But Castiel felt at that moment he deserved to feel a bit of pride. He deserved to just… Push the envelope a tad bit more. He deserved some more care paid to him, some more pampering.

Lord knows when the next time he had enough gall to do this again would be.

And if someone had told him that he was getting carried away, that an almost grown-up man wearing women's lipstick was just as far as this sinful game should go? Well, Castiel would have just tipped his chin up at them and waved goodbye.

Tonight was his night.

That fleck of courage, that want, was what caused him to snatch greedily at his sisters inky black mascara and to paint it painfully along his eyelashes, only dropping the tiny tube twice before he gave up altogether, not wanting to dirty his sisters white floors.

He scooped a crooked finger into the pot of rouge under her mirror, and he helped himself to a small little wooden pencil dipped in brown that he marked with a single line down the back of his mostly hairless legs to give the effect of stockings. All the women now a days were doing it, seeing as how the war effort called for all nylon stockings to be collected for the troops parachutes.

It wasn't long before found that he had kicked off his tan trousers, tweed jacket and pale blue button up shirt in exchange for his mothers cream colored rope of pearls, clattering yellow heels from his older cousin Rachael with her red dress to match, and his sisters rosy halo hat with braided straw and netted crimson veiling.

He looked like a short wild haired nineteen-twenties flapper and he was damn well proud of it.

Yet as he was admiring the flush of his cheeks and the perfect black of his eyelashes, causing his bright blue eyes to sparkle, he didn't notice the sounds of Gabriel's banjo having long since died. Nor the creak of the stairs down the hall. Nor the door of Anna's bedroom being opened by his sister herself.

And when he turned around, breath catching in his throat, and legs feeling so damn bare as they shook from underneath the short dress, he thought he would break down and cry right there.

_Please Anna… Please don't yell at me. Please… _He hoped against hope that she wouldn't.

She never did yell. She never shook him, nor did she glare.

Anna, bless her heart, simply shut the door softly behind her, dragging her pink cushioned chair to hook under the door knob, locking it off to the outside world.

Then, walking up to her little brother who was already about to sob and crumbled into a million pieces, she cupped his face with both of her soft hands and smiled down at him.

"Oh, Castiel - don't you dare cry. You'll mess up your mascara." Her smiled widened as Castiel gave out a dry hiccup, surging foreword and wrapping his arms around the softness of his sister, breathing in her diamond patterned grey sweater.

She hugged him back, encircling him into her arms, allowing Castiel to breathe again, to breathe in the sweet smell of pears and Anna and everything else in her room that screamed with beauty.

They stood there in silence for a good few minutes before Anna released him and set him down on her bed - grabbing her navy blue handkerchief and dabbing under Castiel's red rimmed eyes till the black splotches were all but gone.

Then, with her peach colored fingers she opened up the case of her favorite treasure - her record player that was given to her by their late mother. The needle was poised above the first pitch black record disk - just waiting to be plopped down and rotated. Just waiting to be played.

And play it she did.

All of the sudden Benny Goodman's voice blared into the room that smelled like love and Castiel felt at ease, grabbing his sisters hand as they twirled in their pretty dresses and high heels and laughed till their sides hurt because they could.

After about a half an hour of shaking and swinging and just plain goofing around, Castiel and Anna collapsed on their backs on the floor. Castiel left to admire the bright yellow shoes on his feet that gleamed like something prettier than plastic. Something like gold.

Then, Castiel barely able to catch the words before they left his mouth, mumbled, "Do you suppose Dean thinks I'm nice to look at?".

He almost regretted speaking, saying that question out loud. Almost.

But Anna seemed to understand the quiver in her little brothers voice and so, clearing her own throat, she rolled her head to look at her brother, her bright eyes having such a calming effect on him.

She smiled, a big grin that made Castiel's cheeks flush.

"Why, I know he thinks of you as the prettiest, handsomest boy in town. He's just confused. He's got green eyes only for you Castiel." She assured him, delighting in the happy glow of her brothers eyes as Castiel sighed breathlessly before his own grin curled over his bright red lips.

"Thank you, Anna." Castiel whispered as he gazed at the green ceiling that was flaking in some places.

"No problem, little brother." She whispered back lovingly, taking Castiel's hand in hers as they settled into silence.

…

At the roosters crow Castiel was awoken from his tired sleep. His legs ached from having been strapped into too tall heels all night and he had forgot to brush his teeth - his breath smelling none to pleasant. Oh if only he could go back to sleep.

But he had chores to do and work to accomplish so the littlest Novak shucked himself from the pale blue and white striped quilted covers of his bed to set his feet along the cold wooden floor that burned him like ice.

Grumbling with sleep, he rubbed his eyes and walked to the small little wash bowl on his dresser, splashing water over his face, his wash cloth coming back black, red and white from the makeup that he had slept in.

He smiled down at the smears on the cloth as they were a reminder that what had happened last night was no dream. It was real. _It was progress._

Castiel hummed all the way down stairs, lips still stained slightly from the lipstick. But neither his father nor his brothers bothered to mention it. It was too early on a Saturday morning to be kicking each others teeth out like angry mules.

When Castiel went out to feed the goats and to herd the ewes into the small little barn to be milked before they started bawling with pain, Castiel was joined silently by Dean Winchester who often helped Castiel with his chores seeing as he was a farm hand for hire.

It was a surprised to say the least, to see Dean again, to work side by side with him - but Castiel didn't pay it any mind. That was, until the green eyed boy spoke.

"Mornin', Cas." Dean smiled, those words spoken rather sheepishly, seeing as they were the first words said to the black haired boy in over a month.

"Hello, Dean." Castiel replied softly, not looking into the older boys eyes, feeling his good mood suddenly elevate just a tad. Dean was finally talking to him again after he shared his secret.

It was another half hour before Dean spoke again, this time after they were weeding the garden, (which should have been Anna's chore but Castiel wanted to thank her for last night).

At first he would try to get Castiel to engage in small talk, even addressing Castiel by the fond nickname of _Cas_, but the littlest Novak, still weary, would only nod in answer or keep his replies absolutely short.

But that was until Dean mentioned Castiel's lips.

"Hey Cas, you're mouth sure is awful red. Did you get into a fight with Mike or Luke?" Dean asked as he wiped the sweat from his head with his beaten up leather gloves. He seemed almost worried for the younger boy, and this thought caused Castiel's stomach to flip as he busied himself digging out the roots of a pesky dandelion that would just not budge.

"Um…No. I did not engage in a fight with either of my brothers… I guess I just drank too much cranberry juice at breakfast." Castiel lied, and rather poorly at that.

"A little early in the season for cranberry juice - isn't it?" Dean mused, shiny green eyes focusing just a bit longer on Cas' lips than was appropriate in friendly company.

Castiel blushed a beet red, stuttering to come up with an answer that wouldn't get him mocked or ignored again.

But Dean only chuckled good naturedly and clapped the younger boy on the shoulder, giving it a good squeeze that made Castiel's heart stop for the fewest of seconds.

"Take it easy Cas, I was kidding. Though red really is your color." Dean whispered, lips brushing over Castiel's pinked ears as he leaned in closer, hands lowering themselves to brush against the small of Cas' back.

"You look pretty in it." Chapped lips ghosted over the black haired boys heated flesh before Castiel bit down on his lips to keep from whining. Oh my goodness, he was going to die from blushing.

But then Dean pulled back and smiled all nice and kind and picked up the basket of slightly crumpled weeds that they had gathered, volunteering to dump them in the back pasture. Castiel could go back to the house if he wanted - Dean would do the rest of the chores as an apology for making him flustered.

Castiel could only nod numbly as he watched Dean go, smiling a secret smile to himself as he pondered just how red his face must be.

"Dean Winchester you will be the death of me." He sighed happily before he ran back to the house, the promise of ham sandwiches for lunch with cool ice tea enough to take his mind off things.

…

Next morning, though, a knock on the door was heard down stairs.

It was still early in the morning for the house to be quiet, and seeing as Castiel was the only one up - just finishing a few pages of a book Anna had given to him last December - he hopped downstairs to get the door.

He pulled the curtain back from behind the screened door window to see none other than Dean Winchester in his tan breeches and brown suspenders, shifting from foot to foot and blushing redder than a summer day in July.

Castiel, feeling his throat grow dry, carefully and delicately pulled the door open, mindful that he was still in his bedtime trousers and shirt.

At seeing Castiel's face, Dean's own cheeks blushed pink and he opened his mouth to say something, anything, but nothing came out.

So, thinking better than to garble out some soppy sounding mush, he just pressed a small brown paper package - no bigger than his index finger - into Castiel's palm.

Then Dean, with a nervous tremble that made Cas's eyes widen in confusion, the older boy quickly bent down the slightest bit to brush his lips chastely over Castiel's own, causing an electric shock of nerves and pleasure through the black haired boy.

For a moment, watching as Dean pulled back with a small but shy smile, Castiel felt as if he couldn't breath.

"Dean…I…?" Castiel tried to speak, his voice sounding hoarse as his fingers came to brush against his pink lips, but Dean stopped him, looking to the package instead. "Just… Open it. _Please, _Cas?" Dean struggled to not bolt from his rigid stance on the porch floor boards as his eyes grew glossy and he pulled at the collar of his button up, undoubtedly embarrassed and flustered.

And so Castiel decided to oblige him, tearing at the folds of the package gently before he was greeted with the glossy sheen of a _Max Factor _lipstick tube, brand new and gleaming with a honey gold tube and a perfectly pointed wax red color.

Castiel bit back the tears that threatened to shake through him, feeing his throat close up as he clenched his eyes shut tightly for a few seconds, taking the time to compose himself.

Then, with a sweetened smile on his lips that promised everything was alright, Castiel wrapped his arms around Dean and held him tight - the Winchester's rigid stance not lasting long before Dean melted into the hug as well, pulling Cas tighter to him.

"I'm sorry I ignored you. I was just… It was a lot to be told, y'know? But I just wanted to let you know… if you're okay with it, maybe - we could be sweethearts?" Dean mumbled, into Castiel's neck, smelling Cas' scent and finding that he liked it.

Castiel chuckled softly, his tears threatening to spill again before he nodded into Deans arms, whispering out a pleased albeit hoarse, "I would like nothing more."

And that was how the two found themselves kissing again, a soft brush of lips that felt oh so warm and good before Castiel broke from Deans embrace just for a minute to run into the still silent - thank the Lord for that - household.

He raced into the only bathroom on the first floor and twisted the golden tube of the lipstick between his thumb and finger. He ran it smoothly over his lips before, smacking the color on his mouth, he smiled at his reflection and ran back to his new sweetheart who was sheepishly smiling back at him.

Then, with courage that Castel now found in his heart, he grabbed either side of Dean's face and kissed him hard on the lips, causing the other boy to laugh and kiss back with a fever that had Castiel's heart trembling.

After so many kisses, so many that they lost count, Deans face was peppered with red marks of Cas' lips, all on his forehead and cheeks and even one on his chin and nose. Castiel told him soon he would give Dean a kiss for each and every freckle on the Winchesters face.

But soon Dean had to go back and fix breakfast for his brother and father, so he hugged Castiel goodbye before making his way off the Novak's front porch, giving his new boyfriend a shy little wave, careful not to be seen leaving the farm by anyone else lest their secret be let out.

After watching the boy leave, Castiel sighed pleasantly and turned to go back inside, greeted with the warmth of a house now alive.

As he was walking up the stairs that creaked under his weight, he passed by Gabriel and Anna following the scent of fresh pancakes hissing on the griddle from the kitchen, buttery and warm.

Gabriel paused to look at Castiel's vibrant red lips before he rolled his eyes, fixing his gaze on his younger brother that he loved dearly.

"Do I want to know?" He sighed dully.

Anna and Castiel shared a secret smile of humor before Castiel shook his head, fit to bursting with giggles.

"Right." Gabriel huffed out before he hopped down the stairs, his ears catching Anna and Castiel's loud laughter as he left.

…**.**

**So, Any good? I sure as hell had a blast writing this - it was just so much fun! And as a cross dresser myself, if feels good to indulge yourself in what makes you feel nice. So. REVIEW PLEASE! **


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